CN100999582B - Photosensitive bottom anti-reflective coatings - Google Patents

Photosensitive bottom anti-reflective coatings Download PDF

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CN100999582B
CN100999582B CN2007100051287A CN200710005128A CN100999582B CN 100999582 B CN100999582 B CN 100999582B CN 2007100051287 A CN2007100051287 A CN 2007100051287A CN 200710005128 A CN200710005128 A CN 200710005128A CN 100999582 B CN100999582 B CN 100999582B
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composition
polymkeric substance
layer
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CN100999582A (en
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D·J·古尔瑞罗
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Brewer Science Inc
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/081—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/16—Aliphatic-aromatic or araliphatic polycarbonates
    • C08G64/1608—Aliphatic-aromatic or araliphatic polycarbonates saturated
    • C08G64/1625—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/165—Aliphatic-aromatic or araliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0246—Polyamines containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/026—Wholly aromatic polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/20—Polysulfones
    • C08G75/23—Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31507—Of polycarbonate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Abstract

Anti-reflective compositions and methods of using these compositions to form circuits are provided. The compositions comprise a polymer dissolved or dispersed in a solvent system. Preferred polymers include polycarbonates, polysulfonyl esters, polycarbonate sulfones, and mixtures thereof. The compositions can be applied to a silicon wafer or other substrate to form a cured or hardened layer which is initially insoluble in typical photoresist developing solutions. Upon exposure to light, the cured or hardened layers become soluble in photoresist developing solutions so that the layer can be selectively removed along with the developed photoresist layer, thus eliminating the need for a separate removal step.

Description

The photosensitive bottom anti-reflective coatings
Patent application of the present invention is that international application no is that PCT/US2003/024100, international filing date are on July 28th, 2003, the application number that enters the China national stage is 03818306.4, name is called the dividing an application of application for a patent for invention of " photosensitive bottom anti-reflective coatings ".
Relevant application
The application requires in " the Photosensitive BottomAntireflective Coatings " by name of submission on July 31st, 2002, the right of priority of the temporary patent application of application number No.60/400461, and its reference in content is incorporated in this.
Invention field
The present invention relates to used novel antireflective composition in the manufacturing of photoetching and semiconductor integrated circuit.Specifically, described composition can be dissolved in the time of in being exposed to light in the general development of photoresist solution as bottom anti-reflective coatings.
The background of prior art
The general procedure of removing bottom anti-reflective coatings from base material is wet method and dry process development technology.In wet processing, described bottom anti-reflective coatings is exposed in the alkaline medium that can make polymer dissolution.The bottom anti-reflective coatings of most of wet developables is based on polyamic acid-imide chemistry.That is, acid (dissolving in the alkaline material) is the basis that the ability of described film is removed in control to the conversion of imide (being insoluble in the alkaline matter).This chemical transformation is by thermal initiation, and has a baking window (bake window), and therein, bottom anti-reflective coatings is insoluble in solvent against corrosion, but solvable in alkaline medium.The main difficulty of this technology is maintenance and controls described baking window, avoids occurring scum silica frost (polymer residues), and avoid bottom anti-reflective coatings to be removed by resist.
In dry process development technology, energetic plasma (normally oxygen) can be removed bottom anti-reflective coatings.This technology is fine, but requires extra procedure of processing, and this has increased the cost of manufacturing and output.
Need a kind of improved bottom anti-reflective coatings, it has solved the problem of having to control the baking window, and has cancelled the required additional step of dry process development technology.
Summary of the invention
The bottom anti-reflective coatings of the present invention by new type of polymer being provided and comprising described polymkeric substance overcome these problems.
In more detail, polymkeric substance of the present invention is selected from polycarbonate-based, polysulfonates class, polycarbonate-sulfone class (promptly comprises and having-SO 2With-CO 3The polymkeric substance of repeated monomer).
At described polymkeric substance is in the embodiment of polycarbonate, the preferred polycarbonate-based repeated monomer with following general formula that comprises:
Figure G07105128720070301D000021
In the formula, R 1And R 2Be selected from the functional moieties of glycol separately separately, comprise that aliphatic series (better is C 1-C 12) glycol, aromatics (better be C 4-C 12Two pure and mild heterocycle glycol).Preferred glycol comprises those that are selected from bisphenols.
In a preferred embodiment, R 1And R 2In have a functional moieties (better being bis-phenol P and/or bisphenol Z) that is selected from bisphenols at least.In this embodiment, preferred other R 1And R 2Have following general formula:
Figure G07105128720070301D000022
In the formula, R 5Be that (replacement or unsubstituted better is C to alkyl 1-C 12, be more preferably C 1-C 6), Ar is that (replacement or unsubstituted better is C to aryl at least 4, be more preferably C 4-C 12, be more preferably C 6-C 10).
In another embodiment, work as R 1Or R 2In one of when being the part of dihydroxyphenyl propane, other R 1And R 2Be group group in addition as follows:
Figure G07105128720070301D000023
Especially preferred R 1And R 2Comprise and have those that are selected from following structure:
In this article, term " functional moieties " is meant that its each self-structure changes, make they can with other compound banded compound part.For example, following structure can be thought the functional moieties of dihydroxyphenyl propane:
Figure G07105128720070301D000032
In the described compound original each-hydrogen atom of OH group is removed, make described Sauerstoffatom can and another compound or part link.
At described polymkeric substance is in the embodiment of polysulfonates, and described polymkeric substance better has following general formula:
Figure G07105128720070301D000033
In the formula, X 1Be selected from the functional moieties of two pure and mild dioximes.Preferred glycol comprises that aliphatic series (better is C 1-C 12) glycol, aromatics (better be C 4-C 12) glycol and heterocycle glycol.Especially preferred glycol comprises those that are selected from bis-phenol.Preferred dioxime comprises that aliphatic series (better is C 1-C 12) dioxime, aromatics (better be C 4-C 12) dioxime and heterocycle dioxime.Especially preferred dioxime comprises by condensation aliphatic diamine (NH 2-carbochain-NH 2) and replacement or unsubstituted hydroxy benzaldehyde and glycoloyl benzene and those.An especially preferred example is 1,4-diacetyl benzene dioxime.
In a preferred embodiment, X 1Have general formula-O-Z-O-, in the formula, Z is selected from replacement and unsubstituted aryl (better is at least C 4, be more preferably and be preferably C 4-C 12, to better be C also 6-C 10), replacement and unsubstituted alkyl (are preferably C 1-C 12, be more preferably C 1-C 6) and their combination.Especially preferred X 1Have and be selected from following structure:
Figure G07105128720070301D000041
Figure G07105128720070301D000051
In general formula (II), X 2Be selected from replacement and unsubstituted aryl and (better be at least C 4, be more preferably C 4-C 12, even better be C 6-C 10) and replacement and unsubstituted alkyl (be preferably C 1-C 12, be more preferably C 1-C 6).Especially preferred X 2Comprise and be selected from phenyl, naphthyl, furyl, sulfinyl and anthryl.Preferred X 1And X 2In at least one comprises aromatics part or other extinction group.
At described polymkeric substance is in the embodiment of polycarbonate-sulfone, and the preferred structure of this polymkeric substance is:
In the formula, R 3And R 4Be selected from replacement and unsubstituted aryl separately and (better be at least C 4, be more preferably C 4-C 12, even better be C 6-C 10) and replacement and unsubstituted alkyl (be preferably C 1-C 12, be more preferably C 1-C 6).
R 3And R 4In at least one comprises-SO 2Group, preferred R 3And R 4In at least one comprises aromatics part or other extinction group.Especially preferred R 3And R 4Comprise and be selected from following those:
Figure G07105128720070301D000053
Figure G07105128720070301D000061
Be preferably, the molecular-weight average of described polymkeric substance is about 1000-100000 dalton, is more preferably about 2000-50000 dalton, even is more preferably and is about 2000-20000 dalton.
These polymkeric substance can be used to prepare micro etch method compositions for use (for example, antireflection coating).Described composition better is under the room temperature condition by described polymkeric substance simply is dispersed or dissolved in the suitable solvent systems, forms basically dispersion liquid uniformly after after a while.In the composition total weight as 100 weight %, preferred compositions comprises the polymkeric substance of about 1-20 weight %, better is the polymkeric substance of about 2-10 weight %.
Described solvent systems comprises any solvent that is applicable to the microelectronics manufacturing environment.Preferred solvent systems comprises and is selected from propylene glycol monomethyl ether (PGME), propylene glycol methyl ether acetate (PGMEA), ethyl lactate, propylene glycol, n-propyl ether (PnP), pimelinketone, gamma-butyrolactone and their mixture.In the composition total weight as 100 weight %, the content of described solvent in composition is about 80-98 weight %.Be preferably, the boiling point of described solvent systems is about 100-160 ℃.
Also can be with other composition and described polymkeric substance are distributed in the solvent systems together arbitrarily.The example of other suitable composition comprises linking agent, catalyzer (for example, photic acid forms agent or PAG) and tensio-active agent.Preferred cross-linking agents comprises that aminoplastics (for example, 1174,
Figure G07105128720070301D000063
Product), polyfunctional epoxy resin (for example, MY720, CY179MA, DENACOL), acid anhydrides and their mixture.In in the composition as the total weight of solids of 100 weight %, when using, the content of linking agent in composition is about 10-50 weight %, better is 15-30 weight %.
Suitable PAG comprises ion and nonionic PAG.Especially preferred PAG example comprises sulfonic acid class PAG, those as selling with CGI261, CGI1397 and CGI1311 (CIBA Specialty Chemicals).In in the composition as the total weight of solids of 100 weight %, when using, the content of described PAG in composition is about 0.05-10 weight %, better is to be about 2-8 weight %.
The method of antireflective composition paint base material of the present invention (for example, silicon, aluminium, tungsten, tungsten silicide, gallium arsenide, germanium, tantalum, SiGe and tantalum nitride wafer) is comprised by any conventional method of application (comprising spin coating) (no matter being flat surfaces or the surface that wherein forms through hole or hole) on a certain amount of composition paint substrate surface.Then, described layer should be heated to the crosslinked or solidification value (about 80-180 ℃) of described composition at least, and described layer is solidified or sclerosis, forms thickness and is about 300-
Figure G07105128720070301D000071
(less than the thickness of photoresist layer), described thickness is defined as the mean value of 5 observed values of ellipsometer.
When wavelength was about 193nm, the specific refractory power of described solidified anti-reflection layer or coating (n value) was at least about 1.4, better is about 1.4-1.7.And when wavelength was about 193nm, the OD of cured layer was at least about 2/ micron, better was to be at least about 5/ micron.In other words, be about when described layer
Figure G07105128720070301D000072
The time, described solidified anti-reflection layer absorbs and is at least about 80%, better is to be at least about 90%, is more preferably to be at least about the light that 95% wavelength is about 193nm.
Should be understood that in this stage of described method the solvent (for example, ethyl lactate, propylene glycol methyl ether acetate) that described solidified layer is insoluble to usually basically and photo-resist uses together.And described solidified layer is insoluble to general photoresist developer (for example, alkaline developer is as tetramethyl ammonium hydroxide (TMAH)) basically.In either case, when described layer with after photo-resist solvent or photographic developer contact, described layer variation in thickness is less than about 10%, better less than about 5%, better is about 0%.In this article, percent change is defined as:
Figure G07105128720070301D000073
On the material after photo-resist can paint solidifies, be exposed to required wavelength afterwards (for example, under the light or activating radiation 150-500nm).When being exposed in the light, chemical transformation can take place in described solidified anti-reflection layer, causes described layer to may be dissolved in the typical photoresist developer thus.That is, in this stage, described cured compositions can with conventional water developer such as TMAH and basic metal photographic developer basically (better being complete) remove.In these photographic developers some are buied with trade(brand)name MF-319 (from Shipley, Massachusetts buys), MF-320 (buying from Shipley) and NMD 3 (from TOK, Japan buys).To remove at least about 90% by alkaline developer such as tetramethyl ammonium hydroxide and KOH photographic developer, preferably at least about 99% coating of the present invention.Owing to shortened manufacturing process and reduced its cost, this percent solubility in commercially available photographic developer has superiority than prior art is obvious.
The detailed description of preferred implementation
Embodiment
Following examples have illustrated the preferred method of the present invention.It should be understood that these embodiment only are used for explanation, are used to limit entire area of the present invention anything but.Except as otherwise noted, all material among these embodiment is all buied from Aldrich Chemical Company, and uses with former state.
Embodiment 1
Synthetic polysulfonates
In the present embodiment, prepare polysulfonates of the present invention by condensation aromatic diol and benzene-disulfo-chloride.In this step, (bisphenol S, 1.82g), 1,3-benzene-disulfo-chloride (2.0g) and methylene dichloride (40ml) mix, and at room temperature stir with the alkylsulfonyl xenol in the round-bottomed flask of 100ml.Disposable adding pyridine (1.2ml) to refluxing, keeps described mixture heating up 24 hours.Described reaction is cooled to room temperature, described solvent is concentrated into about 10ml, and polymer deposition is arrived in the methyl alcohol (200ml).Collect the white polymer of 2.73g (83%).FT-IR and ultimate analysis have confirmed described structure.The gained molecular weight is 2747.The structure of resulting polymers is shown in structure A.
Structure A
Figure G07105128720070301D000081
Embodiment 2
Preparation coating
With the polymer dissolution of embodiment 1 preparation in 10ml pimelinketone (4%) solution.Gained solution spin coating (1500rpm) to silicon chip, and 175 ℃ dry 60 seconds down.The membranes submerged of described oven dry is in the TMAH of 0.25N solution, but it can not come off from wafer because of TMAH.Afterwards, described film is exposed in the DUV source, is dissolved in then in the TMAH solution of 0.25N.This shows that described film chemical transformation has taken place being exposed to the DUV light time.That is, in the time of in being exposed to light, described photolytic activity bond rupture, and form sulfonic acid (SO 3H-), cause described polymkeric substance to dissolve in the alkaline material.The general reaction process that shows described chemical transformation is shown in flow process 1.
Determine the optical property of described film, described film is presented at the high absorbance (21.4/ micron of OD) under the 193nm, the medium absorbancy under 248nm (5.6/ micron of OD).This preparation also can carry out modification by adding trimeric cyanamide or glycoluril linking agent (about 25-50 weight %).
Flow process 1
Figure G07105128720070301D000091
In the formula: the R=light absorbing chromophore; X=2 or 3.
Embodiment 3
Polycarbonate synthesis
For example, by making biphenol monomer and the glycol reaction that contains the nitrophenols leaving group, in the backflow chloroform, carry out condensation reaction simultaneously and prepare polymkeric substance of the present invention.People such as White, Synthesis and Characterization ofPhotodefinable Polycarbonates for Use as Sacrificial Materials in theFabrication of Microfluidic Devices, Proc.SPIE, 4690, the 242-253 pages or leaves (2002); People such as Martin, A Convenient Laboratory Preparation of Aromatic Polycarbonates, Polymer Bulletin, 47, the 517-520 pages or leaves (2002), its reference in content is incorporated in this.
In this step, carry out the synthetic of polycarbonate in two steps.At first, the 10ml anhydrous methylene chloride solution with the 2.0g4-chloroformate nitrophenyl ester in 1 hour adds 0.68g 1, in the 0.8ml anhydrous pyridine of 4-xylyl alcohol and the solution of 30ml anhydrous methylene chloride, prepares described monomer thus.Described reaction mixture refluxed is spent the night, and is cooled to room temperature afterwards.The CH that adds capacity 2Cl, with the suspension dissolving that forms, with the described solution of 100ml distilled water wash once, with the 5%HCl solution washing once, and again with distilled water wash once.Described organic layer is dry in sal epsom, filter afterwards, and remove described solvent by rotatory evaporator.Use methylene dichloride and sherwood oil (10: 1) with described white solid product recrystallization, make required monomer thus.
With this monomer (2.0g) and dihydroxyphenyl propane (0.97g), salt of wormwood (2.72g), catalyzer (hexaoxacyclooctadecane-6-6,0.13g) and chloroform (75ml) be blended in the round-bottomed flask of 250ml.Described mixture heating up was refluxed 50 hours.Described reaction mixture is cooled to room temperature, removes by filter inorganic salt, and filtrate is concentrated into about 20ml, and described polymkeric substance precipitates in methyl alcohol (200ml).Collect described white polymer (1.58g, 89%).FT-IR and ultimate analysis have confirmed described structure.Described molecular weight is 5641.The structure of resulting polymers is shown in structure B.
In another step, use other bis-phenol, and obtain higher molecular weight.
Structure B
Embodiment 4
Preparation coating
Polymkeric substance (0.2g) and the CGI 1311 (PAG from CIBASpecialty Chemicals buy) of 0.04g in 14ml PGMEA of embodiment 3 are mixed.Gained solution spin coating (1500rpm) is in silicon chip, and 100 ℃ of down oven dry 60 seconds.The membranes submerged of described oven dry is in the TMAH of 0.25N solution, but it can not come off from wafer because of TMAH.Afterwards, described film is exposed in the DUV source, is dissolved in then in the TMAH solution of 0.25N.This shows that described film chemical transformation has taken place being exposed to the DUV light time.That is, described carbonic acid ester bond and acid (be in this case in being exposed to light time produced by PAG) reaction is decomposed thus and is formed CO 2And alcohol.Described composition becomes and dissolves in the alkaline material.The general reaction process that shows described chemical transformation is shown in flow process 2.
Determine the optical property of described film, described film is presented at the absorbancy height (21.4/ micron of OD) under the 193nm.
Flow process 2
Figure G07105128720070301D000102
In the formula: the R=light absorbing chromophore.
Embodiment 5
Polycarbonate synthesis-sulfone
Prepare similar described in a kind of method of these polymkeric substance and the embodiment 3.
In this step, the same monomer (4.68g) of embodiment 3 preparations and bisphenol S (2.51g), triethylamine (2.79g) and dimethyl aminopyridine (DMAP, 0.14g) reaction in acetonitrile (50ml).Described mixture heating up refluxed 18 hours, was cooled to room temperature then.Described solution concentration to about 15ml, and is precipitated in methyl alcohol (125ml).In vacuum oven, after the dried overnight, collect 2.67g (61%) yellow solid.FT-IR and ultimate analysis have confirmed described structure.The structure of resulting polymers is shown in structure C.
Structure C
Figure G07105128720070301D000111
Embodiment 6
Preparation coating
The polymkeric substance (0.4g) of embodiment 5 preparations is dissolved in the 10ml pimelinketone solution (4%).Gained solution spin coating (1500rpm) is in silicon chip, and 175 ℃ of down oven dry 60 seconds.The membranes submerged of described oven dry is in the TMAH of 0.25N solution, but it can not come off from wafer because of TMAH.Afterwards, described film is exposed in the DUV source, is dissolved in then in the TMAH solution of 0.25N.This shows that described film chemical transformation has taken place being exposed to the DUV light time.That is, in the time of in being exposed to light, described photolytic activity bond rupture, and form sulfonic acid (SO 3H-), cause described carbonic acid ester bond to decompose, and become and dissolve in the alkaline material.The general reaction process that shows described chemical transformation is shown in flow process 3.
Determine the optical property of described film, described film is presented at the absorbancy height (20.6/ micron of OD) under the 193nm.
Flow process 3
In the formula: the R=light absorbing chromophore; X=2 or 3.
Embodiment 7
Synthetic polysulfonates
In the 250ml round-bottomed flask, handle 25ml tetrahydrofuran (THF) (THF) solution of xylyl alcohol (2.82g) with 1M potassium tert.-butoxide solution (41ml), and at room temperature stirred 10 minutes.Then, with 1, (5.62g 25mlTHF) adds in the reaction flask THF solution of 3-benzene-disulfo-chloride in batches.Described mixture heating up was refluxed 24 hours.Then, remove by filter inorganic salt, and remove THF in a vacuum.The gained lingering section is dissolved in the chloroform (12ml) once more, and (150ml) precipitates in methyl alcohol.Filter described settling, and dried overnight in a vacuum.Collect described white solid (0.90g).The structure of resulting polymers is shown in structure D.
Structure D
Figure G07105128720070301D000121
Embodiment 8
Synthetic polysulfonates-oxime
In the 200ml round-bottomed flask, at room temperature, in chloroform (50ml), stir diacetyl benzene oxime (5.66g) and triethylamine (6.00g).Then, with 1,3-benzene-disulfo-chloride (8.08g) adds in the reaction flask in batches.After at room temperature stirring 30 minutes, described mixture heating up was refluxed 24 hours.Described polymkeric substance is separated out from reaction mixture, and collects by filtering.In vacuum oven, after the drying, collect the brown polymkeric substance of 6.0g.The structure of resulting polymers is shown in structure E.
Structure E
Figure G07105128720070301D000122
Embodiment 9
Synthetic polysulfonates-imines
In the present embodiment, all raw materials are all buied from TCI, and use with former state.In 250ml 2 neck round-bottomed flasks, mix N, N-salicyl salicylic acid diplosal aldehyde-1,2-propylene diamine (3.00g), 1,3-benzene-disulfo-chloride (2.92g) and chloroform (40ml), and at room temperature stir.Add triethylamine (2.95ml) in batches, and described mixture heating up was refluxed 23 hours.Described reaction mixture is cooled to room temperature, and described solvent is concentrated into about 15ml, and described polymkeric substance deposits in methyl alcohol (250ml).Collect described polymkeric substance, be dissolved in once more in the chloroform (15ml), and more than in methyl alcohol (200ml), depositing once, in vacuum oven, after the drying, collect the 3.71g yellow polymer.The structure of resulting polymers is as shown in structure F.
Structure F
Figure G07105128720070301D000131
Embodiment 10
Preparation coating
The polymer dissolution that embodiment 9 is made is in the ethyl lactate solution of 10ml 4%.Gained solution spin coating (1500rpm) is to silicon chip, and is and down dry at 150 ℃.The membranes submerged of described oven dry is in the TMAH of 0.25N solution, but it can not come off from wafer because of TMAH.Afterwards, described film is exposed in the DUV source, is dissolved in then in the TMAH solution of 0.25N.This shows that described film chemical transformation has taken place being exposed to the DUV light time, is photosensitive therefore.
Determine the optical property of described film, described film is presented at the absorbancy height (14.4/ micron of OD) under the 193nm, the absorbancy under 248nm medium (5.53/ micron of OD), and therefore, it is suitable for antireflection and uses.
Above preparation also can be by adding trimeric cyanamide or glycoluril linking agent (about 5-50 weight %) and modification is carried out in photic sour formation agent (about 1-10 weight %).

Claims (25)

1. polymkeric substance, it comprises and has the repeated monomer that is selected from following general formula (II):
In the formula,
X 1Be selected from:
Figure FSB00000386618100012
Figure FSB00000386618100021
X 2Be selected from C 6-C 10Aryl and C 1-C 6Alkyl;
X 1And X 2In at least one comprises aromatic group.
2. the described polymkeric substance of claim 1 is characterized in that, described repeated monomer has general formula (II), X 2It is phenyl.
3. antireflective composition, described composition comprises the polymkeric substance that is dispersed or dissolved in the solvent systems, and its improvements are that described polymkeric substance comprises and has the repeated monomer that is selected from following general formula (II):
Figure FSB00000386618100022
In the formula,
X 1Be selected from:
Figure FSB00000386618100031
X 2Be selected from C 6-C 10Aryl and C 1-C 6Alkyl;
X 1And X 2In at least one comprises aromatic group.
4. the described composition of claim 3 is characterized in that, described composition can solidify or harden and form anti-reflection layer, and its thickness is 400
Figure FSB00000386618100041
The time, the wavelength of absorption at least 80% is the light of 193nm.
5. the described composition of claim 3 is characterized in that, the molecular-weight average of described polymkeric substance is 1000-100000 dalton.
6. the described composition of claim 3 is characterized in that, described repeated monomer has general formula (II), X 2It is phenyl.
7. use method for compositions in photo-engraving process, described method comprises on a certain amount of composition paint base material, cambial thereon step, and described composition comprises:
Solvent systems;
Be dispersed or dissolved in the polymkeric substance in the described solvent systems, wherein, described polymkeric substance comprises and has the repeated monomer that is selected from following general formula (II):
Figure FSB00000386618100042
In the formula, X 1Be selected from:
Figure FSB00000386618100043
Figure FSB00000386618100051
X 2Be selected from C 5-C 10Aryl and C 1-C 6Alkyl;
X 1And X 2In at least one comprises aromatic group.
8. the described method of claim 7 is characterized in that, described application step comprises described composition is spun on the described substrate surface.
9. the described method of claim 7 is characterized in that, has formed the hole in the described base material, and described hole is limited by diapire and sidewall, and described application step comprises at least a portion with described diapire of described composition paint and sidewall.
10. the described method of claim 7 is characterized in that, described method also is included in the described layer of oven dry under 80-180 ℃ the temperature, forms to solidify or the step of hardened layer.
11. the described method of claim 10 is characterized in that, after the described baking step, described curing or hardened layer are insoluble in the photoresist developer.
12. the described method of claim 10 is characterized in that, described method also comprises the step on described curing of photo-resist paint or the hardened layer.
13. the described method of claim 12 is characterized in that described method also comprises the steps:
Described at least a portion photo-resist is exposed under the illumination;
Make the development of photoresist of described exposure.
14. the described method of claim 13 is characterized in that, described development step makes described curing or hardened layer come off from the photo-resist adjacent areas of described exposure.
15. the described method of claim 14 is characterized in that, described development step comprises makes described photo-resist contact with alkaline developer with described curing or hardened layer.
16. the described method of claim 10 is characterized in that, described method comprises that also at least a portion with described curing or hardened layer is exposed to the step in the light, and after the described exposing step, described curing or hardened layer dissolve in the photoresist developer.
17. the described method of claim 10 is characterized in that, described composition forms anti-reflection layer, and its thickness is
Figure FSB00000386618100061
The time, the wavelength of absorption at least 80% is the light of 193nm.
18. the described method of claim 7 is characterized in that, described repeating unit has general formula (II), X 2It is phenyl.
19. the described method of claim 7 is characterized in that, described base material is selected from silicon, aluminium, tungsten, tungsten silicide, gallium arsenide, germanium, tantalum, SiGe and tantalum nitride wafer.
20. the front body structure that forms in photo-engraving process, described structure comprises:
Base material with surface;
Anti-reflection layer on described substrate surface, described layer is formed by following composition, and described composition comprises:
Solvent systems;
Be dispersed or dissolved in the polymkeric substance in the described solvent systems, wherein, described polymkeric substance comprises and has the repeated monomer that is selected from following general formula (II):
Figure FSB00000386618100062
In the formula, X 1Be selected from:
Figure FSB00000386618100063
Figure FSB00000386618100071
X 2Be selected from C 6-C 10Aryl and C 1-C 6Alkyl;
X 1And X 2In at least one comprises aromatic group.
21. the described structure of claim 20 is characterized in that, described anti-reflection layer can solidify or harden and form the layer be insoluble to photoresist developer.
22. the described structure of claim 20, described structure also comprise the photo-resist adjacent with described anti-reflection layer.
23. the described structure of claim 20 is characterized in that, described composition can solidify or harden and form anti-reflection layer, and its thickness is The time, the wavelength of absorption at least 80% is the light of 193nm.
24. the described structure of claim 20 is characterized in that, described repeating unit has general formula (II), X 2It is phenyl.
25. the described structure of claim 20 is characterized in that, described base material is selected from silicon, aluminium, tungsten, tungsten silicide, gallium arsenide, germanium, tantalum, SiGe and tantalum nitride wafer.
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Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1673801B1 (en) * 2003-10-15 2014-04-09 Brewer Science, Inc. Developer-soluble materials and methods of using the same in via-first dual damascene applications
CN1934500B (en) * 2004-03-16 2013-03-13 日产化学工业株式会社 Antireflective film containing sulfur atom
US20050255410A1 (en) 2004-04-29 2005-11-17 Guerrero Douglas J Anti-reflective coatings using vinyl ether crosslinkers
US7550249B2 (en) * 2006-03-10 2009-06-23 Az Electronic Materials Usa Corp. Base soluble polymers for photoresist compositions
US7704670B2 (en) 2006-06-22 2010-04-27 Az Electronic Materials Usa Corp. High silicon-content thin film thermosets
JP4831324B2 (en) * 2006-07-06 2011-12-07 日産化学工業株式会社 Resist underlayer film forming composition containing sulfone
US7914974B2 (en) 2006-08-18 2011-03-29 Brewer Science Inc. Anti-reflective imaging layer for multiple patterning process
US7759046B2 (en) * 2006-12-20 2010-07-20 Az Electronic Materials Usa Corp. Antireflective coating compositions
US8026040B2 (en) 2007-02-20 2011-09-27 Az Electronic Materials Usa Corp. Silicone coating composition
KR101523393B1 (en) 2007-02-27 2015-05-27 이엠디 퍼포먼스 머티리얼스 코프. Silicon-based antireflective coating compositions
US20090098490A1 (en) * 2007-10-16 2009-04-16 Victor Pham Radiation-Sensitive, Wet Developable Bottom Antireflective Coating Compositions and Their Applications in Semiconductor Manufacturing
KR101647158B1 (en) 2008-01-29 2016-08-09 브레우어 사이언스 인코포레이션 On-track process for patterning hardmask by multiple dark field exposures
US9640396B2 (en) 2009-01-07 2017-05-02 Brewer Science Inc. Spin-on spacer materials for double- and triple-patterning lithography
CN102781908A (en) * 2010-01-29 2012-11-14 综研化学株式会社 Novel azomethine oligomer
JP5573206B2 (en) * 2010-02-01 2014-08-20 宇部興産株式会社 Polyurethane resin and polyurethane resin composition
US8722840B2 (en) 2010-11-17 2014-05-13 Nissan Chemical Industries, Ltd. Resist underlayer film forming composition, and method for forming resist pattern using the same
JP5933339B2 (en) * 2012-05-23 2016-06-08 東京応化工業株式会社 Resist composition and resist pattern forming method
CN103529649A (en) * 2013-10-07 2014-01-22 吉林大学 Negative fluorine-containing photoresist composition and application thereof in preparation of polymer optical waveguide device

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4175175A (en) * 1963-07-16 1979-11-20 Union Carbide Corporation Polyarylene polyethers
US4320224A (en) * 1977-09-07 1982-03-16 Imperial Chemical Industries Limited Thermoplastic aromatic polyetherketones
US4920200A (en) * 1988-12-27 1990-04-24 General Electric Company Hydroquinone-bisphenol cyclic copolycarbonate oligomer
US4996247A (en) * 1984-02-10 1991-02-26 General Electric Company Enhancing color stability to sterilizing radiation of polymer compositions
US5607824A (en) * 1994-07-27 1997-03-04 International Business Machines Corporation Antireflective coating for microlithography
US5739254A (en) * 1996-08-29 1998-04-14 Xerox Corporation Process for haloalkylation of high performance polymers
US6054254A (en) * 1997-07-03 2000-04-25 Kabushiki Kaisha Toshiba Composition for underlying film and method of forming a pattern using the film
US6359028B1 (en) * 1995-07-12 2002-03-19 Mitsubishi Engineering-Plastics Corporation Polycarbonate resin composition

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE604516A (en) * 1960-06-02
US3615615A (en) * 1970-04-13 1971-10-26 Eastman Kodak Co Photographic emulsions including reactive quaternary salts
US3856751A (en) * 1972-06-14 1974-12-24 Eastman Kodak Co Diacid-xanthylium ion polyester and photographic element comprised thereof
DE2653145A1 (en) * 1976-11-23 1978-05-24 Bayer Ag MOLDING
NL8501838A (en) * 1985-06-26 1987-01-16 Stork Friesland Bv SEMI-PERMEABLE MEMBRANES BASED ON SULPHONATE GROUPS CONTAINING POLYMERS.
JP2562619B2 (en) * 1987-09-29 1996-12-11 ダイセル化学工業株式会社 Polycarbonate copolymer
JPH02259166A (en) * 1988-11-29 1990-10-19 Tonen Corp Sizing agent for reinforcing fiber
JPH03110983A (en) * 1989-09-25 1991-05-10 Sharp Corp Current limit circuit
JP2931353B2 (en) * 1990-01-29 1999-08-09 出光興産株式会社 Polycarbonate copolymer, method for producing the same, and electrophotographic photoreceptor using the same
JPH06266104A (en) * 1993-03-10 1994-09-22 Mitsubishi Rayon Co Ltd Pattern forming composition
JPH06340802A (en) * 1993-05-31 1994-12-13 Sony Corp Photosensitive composition and method for pattern formation
US5691101A (en) * 1994-03-15 1997-11-25 Kabushiki Kaisha Toshiba Photosensitive composition
JPH07278284A (en) * 1994-04-11 1995-10-24 Nippon Steel Chem Co Ltd Copolycarbonate
JPH08110638A (en) * 1994-10-13 1996-04-30 Hitachi Chem Co Ltd Photosensitive resin composition and production of resist image
US5554473A (en) * 1994-11-23 1996-09-10 Mitsubishi Chemical America, Inc. Photoreceptor having charge transport layers containing a copolycarbonate and layer containing same
US6338936B1 (en) * 1998-02-02 2002-01-15 Taiyo Ink Manufacturing Co., Ltd. Photosensitive resin composition and method for formation of resist pattern by use thereof
US6451498B1 (en) * 1998-05-28 2002-09-17 Atotech Deutschland Gmbh Photosensitive composition
US6071662A (en) * 1998-07-23 2000-06-06 Xerox Corporation Imaging member with improved anti-curl backing layer
JP2000111885A (en) * 1998-09-30 2000-04-21 Mitsubishi Chemicals Corp Liquid crystal display element
US6110653A (en) * 1999-07-26 2000-08-29 International Business Machines Corporation Acid sensitive ARC and method of use
KR100520185B1 (en) * 1999-10-11 2005-10-10 주식회사 하이닉스반도체 Novel photoresist polymer and photoresist composition containing it
US20020009599A1 (en) * 2000-01-26 2002-01-24 Welch Cletus N. Photochromic polyurethane coating and articles having such a coating
DE60213593T2 (en) * 2001-05-29 2007-08-02 Essilor International Compagnie Générale d'Optique PROCESS FOR PRODUCING A COATED OPTICAL OBJECT
US6586560B1 (en) * 2001-09-18 2003-07-01 Microchem Corp. Alkaline soluble maleimide-containing polymers
US6916537B2 (en) * 2001-11-01 2005-07-12 Transitions Optical Inc. Articles having a photochromic polymeric coating
US6844131B2 (en) * 2002-01-09 2005-01-18 Clariant Finance (Bvi) Limited Positive-working photoimageable bottom antireflective coating
US7070914B2 (en) 2002-01-09 2006-07-04 Az Electronic Materials Usa Corp. Process for producing an image using a first minimum bottom antireflective coating composition
US20030215736A1 (en) * 2002-01-09 2003-11-20 Oberlander Joseph E. Negative-working photoimageable bottom antireflective coating
US7261997B2 (en) * 2002-01-17 2007-08-28 Brewer Science Inc. Spin bowl compatible polyamic acids/imides as wet developable polymer binders for anti-reflective coatings
KR20030068729A (en) * 2002-02-16 2003-08-25 삼성전자주식회사 Compositions for forming anti-reflective light absorbing layer and method for formimg patterns of semiconductor device using the same
US6911293B2 (en) * 2002-04-11 2005-06-28 Clariant Finance (Bvi) Limited Photoresist compositions comprising acetals and ketals as solvents
US6872506B2 (en) * 2002-06-25 2005-03-29 Brewer Science Inc. Wet-developable anti-reflective compositions
US6740469B2 (en) * 2002-06-25 2004-05-25 Brewer Science Inc. Developer-soluble metal alkoxide coatings for microelectronic applications
KR20040009384A (en) * 2002-07-23 2004-01-31 삼성전자주식회사 Photoresist developer soluble organic bottom anti-reflective composition and photolithography and etching process using the same
US20040077173A1 (en) * 2002-10-17 2004-04-22 Swaminathan Sivakumar Using water soluble bottom anti-reflective coating
US6910718B2 (en) * 2002-12-12 2005-06-28 Nick Chareas Writing pad for cellphone
JP4796498B2 (en) 2003-05-23 2011-10-19 ダウ コーニング コーポレーション Siloxane resin anti-reflective coating composition with high wet etch rate

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4175175A (en) * 1963-07-16 1979-11-20 Union Carbide Corporation Polyarylene polyethers
US4320224A (en) * 1977-09-07 1982-03-16 Imperial Chemical Industries Limited Thermoplastic aromatic polyetherketones
US4996247A (en) * 1984-02-10 1991-02-26 General Electric Company Enhancing color stability to sterilizing radiation of polymer compositions
US4920200A (en) * 1988-12-27 1990-04-24 General Electric Company Hydroquinone-bisphenol cyclic copolycarbonate oligomer
US5607824A (en) * 1994-07-27 1997-03-04 International Business Machines Corporation Antireflective coating for microlithography
US6359028B1 (en) * 1995-07-12 2002-03-19 Mitsubishi Engineering-Plastics Corporation Polycarbonate resin composition
US5739254A (en) * 1996-08-29 1998-04-14 Xerox Corporation Process for haloalkylation of high performance polymers
US6054254A (en) * 1997-07-03 2000-04-25 Kabushiki Kaisha Toshiba Composition for underlying film and method of forming a pattern using the film

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